# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_zcl
_database_code_depnum_ccdc_archive 'CCDC 1486805'
_audit_update_record             
;
2016-06-21 deposited with the CCDC.
2017-01-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H19 Br N4 O2'
_chemical_formula_weight         355.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.1666(10)
_cell_length_b                   12.446(3)
_cell_length_c                   25.390(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1632.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5959
_cell_measurement_theta_min      6.42
_cell_measurement_theta_max      54.92

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    2.528
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'R-AXIS SPIDER'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14756
_diffrn_reflns_av_R_equivalents  0.1165
_diffrn_reflns_av_sigmaI/netI    0.1437
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.21
_diffrn_reflns_theta_max         27.46
_reflns_number_total             3690
_reflns_number_gt                1389
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0341P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.010(14)
_refine_ls_number_reflns         3690
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1708
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1017
_refine_ls_wR_factor_gt          0.0753
_refine_ls_goodness_of_fit_ref   0.829
_refine_ls_restrained_S_all      0.829
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.42728(16) 1.04496(5) 0.22329(3) 0.1128(3) Uani 1 1 d . . .
O1 O 0.5962(8) 0.5524(3) 0.00513(14) 0.0828(11) Uani 1 1 d . . .
N2 N 0.8847(9) 0.4206(3) -0.00996(17) 0.0658(12) Uani 1 1 d . . .
O2 O 0.6734(8) 0.3225(3) 0.08778(15) 0.0854(13) Uani 1 1 d . . .
C7 C 0.8562(9) 0.6715(4) 0.09193(19) 0.0553(14) Uani 1 1 d . . .
N3 N 0.7675(8) 0.5794(3) 0.10569(16) 0.0601(11) Uani 1 1 d . . .
C9 C 0.7605(12) 0.4911(4) 0.0206(2) 0.0616(14) Uani 1 1 d . . .
C4 C 0.5646(14) 0.9300(4) 0.1842(2) 0.0760(16) Uani 1 1 d . . .
C1 C 0.7566(10) 0.7619(4) 0.1236(2) 0.0572(14) Uani 1 1 d . . .
C5 C 0.4744(16) 0.8303(5) 0.1911(2) 0.122(3) Uani 1 1 d . . .
H5A H 0.3446 0.8174 0.2157 0.146 Uiso 1 1 calc R . .
C3 C 0.7488(12) 0.9475(5) 0.1474(3) 0.0990(19) Uani 1 1 d . . .
H3A H 0.8151 1.0164 0.1426 0.119 Uiso 1 1 calc R . .
C10 C 0.7943(12) 0.4097(4) -0.0641(2) 0.088(2) Uani 1 1 d . . .
H10A H 0.6431 0.4533 -0.0692 0.131 Uiso 1 1 calc R . .
H10B H 0.7525 0.3359 -0.0710 0.131 Uiso 1 1 calc R . .
H10C H 0.9280 0.4328 -0.0878 0.131 Uiso 1 1 calc R . .
C8 C 1.0475(11) 0.6923(4) 0.04925(18) 0.0735(15) Uani 1 1 d . . .
H8A H 1.0929 0.6257 0.0325 0.110 Uiso 1 1 calc R . .
H8B H 1.1998 0.7246 0.0640 0.110 Uiso 1 1 calc R . .
H8C H 0.9729 0.7400 0.0237 0.110 Uiso 1 1 calc R . .
C2 C 0.8382(12) 0.8648(4) 0.1170(3) 0.099(2) Uani 1 1 d . . .
H2A H 0.9594 0.8794 0.0909 0.119 Uiso 1 1 calc R . .
N4 N 0.8494(7) 0.4909(3) 0.07415(17) 0.0547(11) Uani 1 1 d . . .
N1 N 0.9678(10) 0.3854(3) 0.14526(19) 0.0724(12) Uani 1 1 d . . .
C11 C 1.1139(11) 0.3616(4) 0.0043(2) 0.0785(16) Uani 1 1 d . . .
H11A H 1.1550 0.3752 0.0405 0.118 Uiso 1 1 calc R . .
H11B H 1.2555 0.3842 -0.0176 0.118 Uiso 1 1 calc R . .
H11C H 1.0840 0.2862 -0.0007 0.118 Uiso 1 1 calc R . .
C14 C 0.9373(15) 0.2904(4) 0.1784(2) 0.112(2) Uani 1 1 d . . .
H14A H 0.7923 0.2491 0.1662 0.168 Uiso 1 1 calc R . .
H14B H 0.9080 0.3123 0.2142 0.168 Uiso 1 1 calc R . .
H14C H 1.0914 0.2475 0.1766 0.168 Uiso 1 1 calc R . .
C13 C 1.1788(11) 0.4582(5) 0.1583(2) 0.104(2) Uani 1 1 d . . .
H13A H 1.1773 0.5180 0.1344 0.156 Uiso 1 1 calc R . .
H13B H 1.3407 0.4208 0.1553 0.156 Uiso 1 1 calc R . .
H13C H 1.1576 0.4838 0.1937 0.156 Uiso 1 1 calc R . .
C6 C 0.5736(15) 0.7466(4) 0.1618(2) 0.104(2) Uani 1 1 d . . .
H6A H 0.5142 0.6773 0.1683 0.125 Uiso 1 1 calc R . .
C12 C 0.8185(12) 0.3929(4) 0.1024(2) 0.0609(15) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.1706(7) 0.0778(4) 0.0900(4) -0.0221(4) -0.0018(5) 0.0379(5)
O1 0.086(3) 0.072(2) 0.090(3) -0.008(2) -0.018(2) 0.026(3)
N2 0.071(3) 0.056(3) 0.070(3) -0.006(2) 0.001(3) 0.012(3)
O2 0.104(3) 0.059(2) 0.093(3) -0.002(2) 0.003(2) -0.024(2)
C7 0.055(4) 0.046(3) 0.064(4) 0.004(3) 0.002(3) -0.002(3)
N3 0.061(3) 0.048(3) 0.072(3) -0.008(2) 0.007(2) 0.002(2)
C9 0.058(4) 0.050(3) 0.077(4) 0.000(3) -0.003(3) -0.011(3)
C4 0.115(5) 0.051(4) 0.062(3) -0.009(3) -0.008(4) 0.021(4)
C1 0.071(4) 0.037(3) 0.063(4) 0.001(2) -0.007(3) 0.001(3)
C5 0.198(8) 0.059(4) 0.109(5) -0.005(4) 0.075(6) 0.006(5)
C3 0.099(5) 0.054(4) 0.144(6) -0.021(4) 0.016(5) -0.008(4)
C10 0.110(5) 0.081(5) 0.071(4) -0.002(3) 0.002(4) 0.013(4)
C8 0.072(4) 0.062(3) 0.086(4) 0.004(3) 0.014(4) -0.006(3)
C2 0.104(5) 0.051(4) 0.143(6) -0.009(4) 0.053(4) -0.005(3)
N4 0.057(3) 0.043(2) 0.064(3) -0.003(2) 0.000(2) -0.001(2)
N1 0.084(4) 0.055(3) 0.078(3) 0.005(2) -0.001(3) 0.008(3)
C11 0.068(4) 0.074(4) 0.094(4) -0.011(3) 0.014(4) 0.002(3)
C14 0.173(7) 0.089(4) 0.075(4) 0.025(3) 0.020(5) 0.024(5)
C13 0.087(5) 0.118(5) 0.107(5) -0.006(4) -0.028(4) 0.007(5)
C6 0.174(7) 0.054(4) 0.084(4) 0.001(3) 0.056(5) -0.005(4)
C12 0.067(4) 0.046(4) 0.069(4) -0.001(3) 0.010(3) 0.001(3)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C4 1.881(5) . ?
O1 C9 1.207(6) . ?
N2 C9 1.336(6) . ?
N2 C11 1.439(6) . ?
N2 C10 1.459(6) . ?
O2 C12 1.212(6) . ?
C7 N3 1.282(5) . ?
C7 C1 1.475(6) . ?
C7 C8 1.489(6) . ?
N3 N4 1.427(5) . ?
C9 N4 1.435(6) . ?
C4 C5 1.337(7) . ?
C4 C3 1.352(7) . ?
C1 C2 1.359(6) . ?
C1 C6 1.369(7) . ?
C5 C6 1.379(7) . ?
C3 C2 1.367(7) . ?
N4 C12 1.424(6) . ?
N1 C12 1.337(7) . ?
N1 C13 1.455(6) . ?
N1 C14 1.459(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N2 C11 125.8(5) . . ?
C9 N2 C10 117.1(5) . . ?
C11 N2 C10 116.9(4) . . ?
N3 C7 C1 114.1(4) . . ?
N3 C7 C8 126.2(5) . . ?
C1 C7 C8 119.7(4) . . ?
C7 N3 N4 115.5(4) . . ?
O1 C9 N2 124.3(5) . . ?
O1 C9 N4 122.4(5) . . ?
N2 C9 N4 113.3(5) . . ?
C5 C4 C3 119.2(5) . . ?
C5 C4 Br1 120.3(5) . . ?
C3 C4 Br1 120.5(5) . . ?
C2 C1 C6 115.6(5) . . ?
C2 C1 C7 122.9(5) . . ?
C6 C1 C7 121.4(5) . . ?
C4 C5 C6 120.0(6) . . ?
C4 C3 C2 120.4(6) . . ?
C1 C2 C3 122.4(6) . . ?
C12 N4 N3 110.2(4) . . ?
C12 N4 C9 116.3(4) . . ?
N3 N4 C9 115.8(4) . . ?
C12 N1 C13 124.9(5) . . ?
C12 N1 C14 117.6(5) . . ?
C13 N1 C14 117.0(5) . . ?
C1 C6 C5 122.3(5) . . ?
O2 C12 N1 123.7(5) . . ?
O2 C12 N4 122.3(6) . . ?
N1 C12 N4 113.9(5) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.045
